33079-11-7

Usage

InChI:InChI=1/C15H15NO3/c17-14-12-4-2-1-3-11(12)5-6-13(14)15(18)16-7-9-19-10-8-16/h1-6,17H,7-10H2

Upstream product

• 347370-63-2 C₁₅H₁₅NO₃ 
• 110-91-8 morpholine 
• 38077-69-9 1-hydroxy-2-naphthoyl chloride 
• 86-48-6 1-hydroxy-2-naphthoic acid 

Downstream Products

• 1346166-53-7 (1-hydroxy-4-(phenyldiazenyl)naphthalen-2-yl)(morpholin-4-yl)methanone 

Relevant academic research and scientific papers

Switching azonaphthols containing a side chain with limited flexibility. Part 1. Synthesis and tautomeric properties

A series of azo dyes, possessing amide fragments with restricted flexibility tethered to 4-(phenyldiazenyl)naphthalen-1-ol, was obtained from 1-hydroxy-2-naphthoic acid by subsequent conversion to amides and diazo coupling. It was shown that the position of the tautomeric equilibrium in solution strongly depends on the solvent in both UV and NMR concentration scale. The compounds exist as pure enol forms in chloroform and hydrocarbons, while in polar solvents (acetone, acetonitrile, alcohols) a tautomeric mixture is observed. According to the quantum-chemical calculations the aggregation of the keto tautomer is the possible reason for this shift in the position of the tautomeric equilibrium. To support the theoretical predictions, it was found that from acetone the keto form crystallizes as a dimer with hydrogen bonding between N1-H in the one molecule and amide CO in the other forming a three-dimensional structure. The importance of the side-chain nitrogen atom on the dimer formation was confirmed by solution and solid state study of 4-(phenyldiazenyl)-2-acetylnaphthalen-1-ol. The results indicate that the new azo-dyes obtained could be suitable candidates for switching and sensing applications in non-polar solvents.

Anionic ortho-fries rearrangement, a facile route to arenol-based mannich bases

Phenol and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90 C, under a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-[(dialkylamino)methyl]-8- hydroxy-1-naphthaldehydes is presented.